Four Times Derek Almost Proposed And One He Did
by troatie
Summary: Just a fluffy Addek oneshot. Four Times Derek Almost Proposed And One He Did .


Disclaimer: They aren't mine.

A/N: Written for a challenge with the prompt "sightseeing".

* * *

**Four times Derek almost proposed (and one he did).**

"_A –_

_How about we take a break from studying and go out tonight?_

_Wear something pretty (I'm wooing you)._

_Love, D._

_P.S: Be ready at six."_

It all starts with the post-it she finds when she gets home that Saturday. She has an exam next week – the last one before she can officially call herself Dr. Addison Forbes Montgomery – and she's barely seen her boyfriend in days. Between school and studying – Derek studies with Mark and Addison prefers to do it alone – they really don't have time to hang out, so the date is a welcome distraction from all the hard work of the last weeks of med school.

Addison smiles when she opens the door and sees him standing there, wearing the suit she had to almost force to buy when they went to Nancy's wedding – Derek considered jeans to be just fine for every occasion – and shooting her that smile of his that always made her feel like she was the only woman in the world. He leads her towards the cab after placing a small kiss on her lips and opens the door for her, determined to make the date as perfect as possible.

_**---**_

A bright smile appears on Addison's face when Derek reaches for her hand across the table after they're done eating. She can't remember the last time they went on a fancy date, and she's enjoying the change from their usual Chinese take-out nights. Not that she doesn't love their casual dates, but... well, fancy is very nice from time to time.

Derek slides his hand into his pocket and lets his fingers toy nervously with the small box inside. The ring – the perfect ring that he found after weeks of dragging Mark from jewelry shop from jewelry shop – is waiting for him to take it out and show it to her after popping the question, but somehow, he isn't ready yet.

She's smiling at him, one of those smiles that take his breath away, and she's wearing his favorite black dress and shoes. They're sitting at a table on the River Café, with a privileged view of the Manhattan skyline, and the night is absolutely perfect. And yet, something's not right. It's not the perfect moment. So, after the awkward pause that follows an "Addison, I...", he smiles and tells her he loves him, his hand leaving the box in his pocket and joining hers on the table.

_**--- **_

Derek can't help but smile when he wraps his arms around her waist and softly kisses her neck, locks of auburn hair tickling his face as he breathes her in. Addison is leaning against the railing of the ferry, looking at the calm water below. It was Mark's idea to propose here, because, in his own words, "Derek has a thing for ferryboats, and he also has a thing for Addie, so... perfect scenario." And Derek really can't disagree.

He's holding the woman he loves, her familiar scent clouding his mind as it always does, and her head resting on his shoulder, letting him feel her breathing on his neck. The night is warm enough to enjoy being on the deck, and the view from the ferry – Brooklyn or Manhattan depending on which way they look – couldn't be better. But it's not the right moment.

Addison knows something's not right. Derek is being quiet, and he seems to be thinking of something else all the time, which isn't like him. She assumes he's stressed out because of their exams – it's his final exam too, after all – and shrugs it off. "Addie?" his voice makes her look up to meet his eyes, but – for the second time tonight – he stays quiet after saying her name, making her worries come back to her mind. But he kisses her before she can ask what's wrong, and she soon forgets about everything but Derek's lips on hers.

**_--- _**

If she has to be completely honest, Addison thinks this is too cheesy, even for Derek Shepherd. She knows her boyfriend can be old-fashioned and even a bit too romantic sometimes, but she really wasn't expecting him to take her on a carriage ride in Central Park. Not that she didn't appreciate the gesture – he really was wooing her tonight – but she wasn't really comfortable with the cliché romantic gestures, and she thought he knew it by now.

But Addison can't really focus on how cheesy this moment is much longer, because Derek wraps his arm around her shoulders and pulls her towards him, placing a chaste kiss on her temple and making her remember why she doesn't mind romance from time to time. She snuggles into his side, letting him hold her closer, and she thinks there's nowhere else she'd rather be, even if carriage rides are still awfully cheesy.

Derek knew this wasn't going to be the perfect moment even before he saw Addison hesitate before getting on the carriage. He knows Addison isn't the kind of girl who likes that kind of gestures, but he had to give it a try. Weiss had proposed to Savvy in one of these, and it'd worked for him, right? Derek pats the small box throught the fabric of his pants, as if he needs to make sure it's still there. He can only hope his last idea – his secret weapon, if you will – will work out.

**_--- _**

"No peeking." Derek's breath tickles her skin as he whispers in her ear. She knows they're in an elevator, but that's all she knows right now. Derek made her close her eyes when they were still in the cab, and his hands went to her eyes as soon as they stepped out of the car, saying it was a surprise. And Addison would have said she hates surprises – because she does – but she also knows, when it's Derek planning them, surprises are always good.

Addison gasps when Derek's hands finally move from her eyes to rest on her hips, his chin resting on her shoulder, and she sees the whole city at her feet. The view from the Empire State – her favorite spot in Manhattan – always takes her breath away, no matter how many times she's seen it already. After a moment, she turns around an kisses him softly, silently thanking him for taking her there.

Derek's hand is in his pocket, holding the ring. He's waiting for her to ask for a quarter for the cute little viewfinders – as she always does when they're up here – and his plan is to slip the ring into her hand instead of the quarter and pop the question right then. But he changes his mind in the last moment, because something isn't right. He doesn't know what it is, really. Addison's smile is brighter than it's been in days, they're standing on her favorite spot, overlooking Manhattan, and it has all the ingredients to be the perfect moment. But, somehow, it isn't. And so, he reaches into his other pocket to give her a real quarter when she asks, smiling at her when she excitedly looks for their apartment with the viewfinder.

**_--- _**

Derek sighs when they get home, still trying to wrap his mind around the uselessness of their date. Four ideas – four ideas, for God's sakes! – and none of them had worked out. He can't believe it. At this rate, he's never going to propose. And he wants to, he really does. He just wants to do it in the perfect moment. One of those moments – that happen more often every day – when he thinks he'll die if he can't wake up next to her every day for the rest of his life. Apparently, though, now that he has finally found the perfect ring, those perfect moments aren't going to happen any time soon.

As Derek takes off his tie and shoes, Addison walks into the bathroom, still worried about him. The date, as far as she's concerned, was absolutely perfect – carriage included, because it went well with the touristic theme of the night – and yet he looks like he's angry at everything and everyone in the world. Addison really doesn't get it. But she tells herself it's the exams and takes off her dress and make-up, slipping on one of his t-shirts and letting her hair down to get into bed. She walks back into their bedroom and sees he still hasn't undressed and he's sitting on their bed, seemingly deep in thought.

Derek smiles the moment he sees her next to him. "I had an amazing time tonight." And he knows she means it, because she doesn't know what almost happened – four times! – but never did. He smiles at her before replying "Even though it was like the ultimate tour of NYC for tourists?" She chuckles slightly and kisses him softly. "The sightseeing was the best part." And that's when he knows.

When he looks at her – ratty t-shirt that's far too big for her, no make-up and slightly messy hair – sitting on their bed – which has been undone for days, by the way – and looks around to take in the mess of clothes, books and papers that is their room, he knows.

"Marry me." He shows her the ring when she looks at her with a shocked expression on her face. "Addison Forbes Montgomery, will you marry me?" And she doesn't answer, but the kiss definitely feels like a yes. He smiles when they finally pull away, and thinks she looks even more beautiful when her eyes are sparkling with both happiness and tears. "You know, you have to say yes to get the ring." And he laughs before she whispers her answer and he slips the ring on her finger, thinking this moment was definitely worth all the cheesy sightseeing.


End file.
